EP0957136B1 - Additif pour pigment comprenant des composés disazoiques et compositions pigmentaires le contenant - Google Patents

Additif pour pigment comprenant des composés disazoiques et compositions pigmentaires le contenant Download PDF

Info

Publication number
EP0957136B1
EP0957136B1 EP99108579A EP99108579A EP0957136B1 EP 0957136 B1 EP0957136 B1 EP 0957136B1 EP 99108579 A EP99108579 A EP 99108579A EP 99108579 A EP99108579 A EP 99108579A EP 0957136 B1 EP0957136 B1 EP 0957136B1
Authority
EP
European Patent Office
Prior art keywords
disazo
pigment
disazo pigment
acetoacetic acid
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP99108579A
Other languages
German (de)
English (en)
Other versions
EP0957136A3 (fr
EP0957136A2 (fr
Inventor
Hirohito Ando
Shigeto Aoki
Sadayuki Tomioka
Nagatoshi Kobayashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
Dainippon Ink and Chemicals Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dainippon Ink and Chemicals Co Ltd filed Critical Dainippon Ink and Chemicals Co Ltd
Publication of EP0957136A2 publication Critical patent/EP0957136A2/fr
Publication of EP0957136A3 publication Critical patent/EP0957136A3/fr
Application granted granted Critical
Publication of EP0957136B1 publication Critical patent/EP0957136B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0055—Mixtures of two or more disazo dyes

Definitions

  • the present invention relates to an additive for a disazo pigment, comprising a disazo compound mixture; and a pigment composition. More specifically, the present invention relates to (1) an additive for a pigment, comprising a disazo compound mixture, that is capable of producing a printing ink with a superior flow ability; and (2) a pigment composition capable of producing printing ink with a superior flow ability.
  • Japanese Patent Application, Second Publication No. Sho 45-11026 discloses a method for mixing sulfonic acid compounds into disazo pigments
  • Japanese Patent Application, Second Publication No. Sho. 55-49087 discloses a method for using a disazo pigment formed by using a mixture of non-polar coupling components and polar coupling components having carboxyl groups and/or sulfo groups as coupling components
  • Sho 63-178169 respectively disclose a method of using a disazo pigment composition containing asymmetric disazo compounds which are formed from polar coupling components and non-polar coupling components, respectively.
  • a disazo pigment composition disclosed in Japanese Patent Application, First Publication No. Sho 63-178169 is more effective in improving the flow ability of printing inks.
  • Japanese Patent Application, First Publication, No. Hei 4-275373 discloses a rosin surface-treated pigment, wherein a disazo compound mixture is formed by means of reacting 2 to 40 mol% of acetoacetic acid m-xylidide, 97.9 to 60 mol% of acetoacetic acid o-toluidide, and 0.1 to 10 mol% of 2-acetoacetylamino benzoic acid, as the coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • the objects of the present invention relate to (1) a composition, comprising a disazo compound mixture, that is capable of producing a printing ink with a superior flow ability; (2) a pigment composition capable of producing a printing ink with a superior flow ability; and (3) a printing ink with a superior flow ability.
  • the inventors of the present invention have achieved the present invention, as a result of intense research efforts for developing a printing ink with a superior flow ability. As a result, they have developed (1) an additive for a pigment, comprising a disazo compound mixture, that is capable of producing a printing ink with a superior flow ability; and (2) a pigment composition capable of producing a printing ink with a superior flow ability.
  • the present invention provides the following.
  • the additive for a disazo pigment according to the present invention contains at least the aforementioned compounds represented by Formulae (I), (IV), and (V). These three components, which respectively comprise asymmetric chemical structures, are essential components contributing to an improvement of the flow ability of a printing ink containing the pigment.
  • composition comprising a disazo compound mixture according to the present invention, can be used as an additive for a disazo pigment, and the aforementioned three components consisting of, for example, acetoacetic acid m-xylidide, acetoacetic acid o-toluidide, and 2-acetoacetylamino benzoic acid can be used as coupler components.
  • the composition is able contain the compounds represented by the above Formulae (I), (IV), and (V).
  • the mixing ratio of the three components is not particularly limited, however, a ratio of 39 - 47 mol% of acetoacetic acid m-xylidide to 11 - 19 mol% of acetoacetic acid o-toluidide to 38 - 46 mol% of 2-acetoacetylamino benzoic acid is preferred.
  • a disazo compound mixture which is used to adjust the disazo pigment composition disclosed in Japanese Patent Application, First Publication, No. Sho. 63-178169, is characterized in comprising two components consisting of acetoacetic acid m-xylidide and 2-acetoacetylamino benzoic acid, as coupler components, or alternatively, acetoacetic acid o-toluidide and 2-acetoacetylamino benzoic acid, as coupler components.
  • a compound represented by Formula (I) is not contained therein.
  • the additive for a pigment according to the present invention contains a compound represented by the above Formula (I).
  • the composition comprising a disazo compound mixture according to the present invention, possesses fine crystal particles (grains) with little aggregative property between these crystal particles. Thus, it is easy to disperse the composition at the primary particle level, in the process of producing a lithographic ink. Accordingly, the composition comprising a disazo compound mixture can be adsorbed uniformly and firmly to the surface of a disazo pigment, thereby providing the resultant printing ink with a superior flow ability, in response to a high-speed printing machine.
  • the disazo compound mixture which is used to adjust the disazo pigment composition, disclosed in Japanese Patent Application, First Publication, No. Sho. 63-178169, possesses large crystal particles, with a large amount of aggregative property between these crystal particles.
  • the disazo compound mixture cannot be adsorbed uniformly and firmly to the surface of a disazo pigment, and thus is not capable of producing a printing ink with a superior flow ability, in response to a high-speed printing machine.
  • the additive for a disazo pigment according to the present invention can be obtained by means of reacting acetoacetic acid m-xylidide, acetoacetic acid o-toluidide, and 2-acetoacetylamino benzoic acid, as coupler components, with a tetrazo component, wherein a greater amount of the disazo compound represented by the aforementioned formula (V) is contained than the disazo compound represented by the aforementioned formula (IV).
  • said additive can be formed by means of reacting 39 to 47 mol% of acetoacetic acid m-xylidide, 11 to 19 mol% of acetoacetic acid o-toluidide, 38 to 46 mol% of 2-acetoacetylamino benzoic acid, as coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as a tetrazo component.
  • the composition comprising the disazo compound mixture can be manufactured, for example, according to the following manufacturing method.
  • the term "mol%" indicates the proportional content of the 3-type coupler component formed from 2-acetoacetylamino benzoic acid, acetoacetic acid m-xylidide, and acetoacetic acid o-toluidide.
  • the disazo compound mixture obtained in this manner is a mixture comprising six disazo compounds possessing the respective chemical structures shown below.
  • the six-type disazo compound may also be obtained by means of mixing the aforementioned disazo compounds separately; however, the crystal particles of a mixture comprising six types of disazo compounds formed by means of reacting 39 to 47 mol% of acetoacetic acid m-xylidide, 11 to 19 mol% of acetoacetic acid o-toluidide, and 38 to 46 mol% of 2-acetoacetylamino benzoic acid, as the coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component, are finer and possess a low aggregative property between particles, such that at the time of manufacturing the lithographic ink, it is possible to easily disperse the mixture, all the way down to the level of the primary particles.
  • This process is preferable, since the formation of primary particles from the mixture comprising six types of disazo compounds produces the effects of facilitating a sharp particle size distribution of the crystal particles, as well as a low aggregative property between crystal particles. In contrast, the crystal primary particles obtained from only a single type of disazo compound results in a different grain diameter for each of the six types of disazo compounds, such that the aforementioned superior effects are not obtained.
  • composition formed from a mixture comprising six types of disazo compounds formed by means of reacting 39 to 47 mol% of acetoacetic acid m-xylidide, 11 to 19 mol% of acetoacetic acid o-toluidide, and 38 to 46 mol% of 2-acetoacetylamino benzoic acid, as the coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component, as the pigment composition itself, it is preferable to use the aforementioned composition as a pigment composition after adding a separately prepared disazo pigment.
  • the aforementioned mixture of the six types of disazo compounds is not treated with a rosin.
  • Any conventionally used compound may be employed as the disazo pigment used in the present invention.
  • a mixed crystal of a disazo pigment disclosed in Japanese Patent Application, Second Publication No. Sho 48-26373 e.g., a mixed crystal of a disazo pigment formed by means of reacting a mixed coupler component, comprising acetoacetic acid m-xylidide and acetoacetic acid o-toluidide, with a tetrazo compound of 3,3'-dichlorobenzidine, as the coupler components; and (4) a disazo pigment formed from a disazo compound represented by the aforementioned Formula (I).
  • disazo pigment for use in the present invention, from the major perspective of improving the flow ability, it is preferable to have at least one disazo pigment selected from the group consisting of C.I. Pigment Yellow 13, C.I. Pigment Yellow 14, and a disazo compound represented by the aforementioned Formula (I).
  • This disazo pigment may be formed from a mixture of two or more types of disazo pigments each respectively comprising a single type of disazo compound; however, mixed crystals of the aforementioned are particularly preferred.
  • the disazo pigment described concretely above is a disazo pigment formed by means of reacting at least one type of coupler component selected from the group consisting of acetoacetic acid m-xylidide, acetoacetic acid o-toluidide, acetoacetic acid p-toluidide, and acetoacetic acid anilide, with a tetrazo component comprising a tetrazo compound of 3,3'-dichlorobenzidine.
  • the disazo pigment formed by means of reacting a mixed coupler component comprising acetoacetic acid m-xylidide and acetoacetic acid o-toluidide, with a tetrazo component, comprising a tetrazo compound of 3,3'-dichlorobenzidine is a disazo pigment containing all of the aforementioned disazo compounds of C.I. Pigment Yellow 13, C.I. Pigment Yellow 14, and a disazo compound represented by the aforementioned Formula (I).
  • Another preferred disazo pigment is one that includes a disazo compound represented by the aforementioned Formula (III), as an essential component.
  • This is a disazo pigment formed by means of reacting acetoacetic acid m-xylidide, as an essential coupler component, with the a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a preferred composition includes a composition that is formed by means of reacting a mixed coupler component, comprising 10 to 90 mol% of acetoacetic acid m-xylidide and 10 to 90 mol% of acetoacetic acid o-toluidide, as the coupler components, as this results in maximal improvement in the flow ability; while a composition that is formed by means of reacting a mixed coupler component, comprising 60 to 80 mol% of acetoacetic acid m-xylidide and 20 to 40 mol% of acetoacetic acid o-toluidide, as the coupler components, is particularly preferred, as this results in the highest transparency and clearest printed material when used in a lithographic ink.
  • the disazo pigment for use in the present invention can be manufactured, for example, according to the following manufacturing method.
  • a nonionic surface active agent for the purpose of improving the dispersibility of the disazo pigment, it is possible to carry out surface treatment using any of the following: a nonionic surface active agent, a cationic surface active agent, an anionic surface active agent, a resin, and rosin.
  • surface treatment using rosin is preferred from the standpoint of significantly improving the dispersibility, and additionally improving the transparency thereof.
  • a pigment composition according to the present invention one comprising a rosin-treated disazo pigment, and a rosin-untreated composition comprising a disazo compound mixture, formed by means of reacting 39 to 47 mol% of acetoacetic acid m-xylidide, 11 to 19 mol% of acetoacetic acid o-toluidide, and 38 to 46 mol% of 2-acetoacetylamino benzoic acid, as the coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component, is preferred.
  • This pigment composition according to the present invention provides a flow ability which is superior to that of a conventional disazo pigment used "as it is", i.e., using a pigment composition prepared by treating the surface of a disazo compound mixture with a rosin as the "disazo pigment” itself, the disazo compound being formed by means of reacting 2 to 40 mol% of acetoacetic acid m-xylidide, 97.9 to 60 mol% of acetoacetic acid o-toluidide, and 0.1 to 10 mol% of 2-acetoacetylamino benzoic acid, as the coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • the proportional content of the disazo pigment comprises 85 to 99% by weight of the disazo pigment and 1 to 15% by weight of the composition formed from the aforementioned disazo compound mixture, and preferably 93 to 97% by weight of the disazo pigment and 3 to 7% by weight of the composition formed from the aforementioned disazo compound mixture.
  • the improvement in the flow ability decreases as the proportional content of the composition formed from the aforementioned disazo compound mixture is decreased; while the tinting strength of the pigment decreases as the proportional content of the composition formed from the aforementioned disazo compound mixture is increased.
  • the printing ink containing the pigment composition according to the present invention may be manufactured, for example, according either of the processes below.
  • the dispersing apparatus there can be mentioned, for example, a triple-roll mill, beads mill, kneader, and the like.
  • Examples of the aforementioned varnish include a mixture comprising a resin, such as a rosin-modified phenol resin, petroleum resin, alkyd resin, or a drying oil-modified resin of the aforementioned resins; and when necessary, plant oils such as linseed oil, tung oil, soybean oil, and the like; and a solvent, such as n-paraffin, isoparaffin, aromatic, naphthene, ⁇ -olefin, and the like.
  • a varnish containing an acrylic acid ester can also be mentioned.
  • additives such as ink solvents, dryers, leveling agents and thickeners may also be appropriately blended into the printing ink containing the disazo pigment composition of the present invention, as needed.
  • the resultant slurry was stirred for one hour, heated to 90°C, and then stirred again for an additional two hours.
  • the resultant mixture was then filtered and washed with water to obtain a wet cake of a disazo compound mixture.
  • the wet cake was subsequently dried at 90°C and ground to yield a disazo compound mixture in powder form (Disazo Compound Mixture 1).
  • This disazo compound mixture corresponded to a disazo compound mixture obtained by reacting 42 mol% of acetoacetic acid m-xylidide, 18 mol% of acetoacetic acid o-toluidide, and 40 mol% of 2-acetoacetylamino benzoic acid, as the coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a disazo compound mixture was manufactured according to a method for manufacturing disazo pigment compounds disclosed in Japanese Patent Application, First Publication, No. Sho 63-178169.
  • a concrete manufacturing method is described in the following.
  • a disazo compound mixture (Comparative Disazo Compound Mixture 2) was obtained, in the same manner as in the manufacturing of the disazo compound mixture according to Disazo Compound Mixture Manufacturing Comparative Example 1, with the exception that 31.0 parts of acetoacetic acid m-xylidide was used instead of 28.8 parts of acetoacetic acid o-toluidide.
  • a disazo compound mixture (Comparative Disazo Compound Mixture 3) was obtained, by means of mixing 28.6 parts of Comparative Disazo Compound Mixture 1 and 71.4 parts of Comparative Disazo Compound Mixture 2.
  • the tetrazo solution was added to this suspension, over the course of two hours, during which time, the temperature of the reaction liquid was maintained at 15 to 17°C. After further stirring the reaction liquid for one hour, the reaction liquid was adjusted to a pH of 12 using an aqueous solution of sodium hydroxide. Rosin, which had been dissolved in an aqueous solution of sodium hydroxide (equivalent of 100 parts of rosin), was then added thereto. The resultant mixture was heated to 90°C, and then stirred for two hours. Subsequently, 75 parts of 35% calcium chloride was added, and the mixture was stirred for an additional hour.
  • the resultant mixture was then filtered and washed with water to obtain a press cake of a disazo pigment.
  • the press cake was subsequently dried at 90°C and ground to yield a powdered disazo pigment (Disazo Pigment 1).
  • This disazo pigment corresponded to a rosin-treated, disazo pigment (C. I. Pigment Yellow 13) obtained by reacting 100 mol% of acetoacetic acid m-xylidide as the coupler component, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • C. I. Pigment Yellow 13 a rosin-treated, disazo pigment obtained by reacting 100 mol% of acetoacetic acid m-xylidide as the coupler component, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a powdered disazo pigment (Disazo Pigment 2) was obtained, in the same manner as in the manufacturing of a disazo pigment according to Disazo Pigment Manufacturing Example 1, with the exception that 332.2 parts of acetoacetic acid m-xylidide and 77.4 parts of acetoacetic acid o-toluidide were used, instead of the 415 parts of acetoacetic acid m-xylidide.
  • This disazo pigment corresponded to a rosin-treated, disazo pigment (including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)), obtained by reacting 80 mol% of acetoacetic acid m-xylidide and 20 mol% of acetoacetic acid o-toluidide, as the mixed coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a rosin-treated, disazo pigment including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)
  • a powdered disazo pigment (Disazo Pigment 3) was obtained, in the same manner as in the manufacturing of a disazo pigment according to Disazo Pigment Manufacturing Example 1, with the exception that 311.5 parts of acetoacetic acid m-xylidide and 96.7 parts of acetoacetic acid o-toluidide were used, instead of the 415 parts of acetoacetic acid m-xylidide.
  • This disazo pigment corresponded to a rosin-treated, disazo pigment (including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)), obtained by reacting 75 mol% of acetoacetic acid m-xylidide and 25 mol% of acetoacetic acid o-toluidide, as the mixed coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a rosin-treated, disazo pigment including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)
  • a powdered disazo pigment (Disazo Pigment 4) was obtained, in the same manner as in the manufacturing of a disazo pigment according to Disazo Pigment Manufacturing Example 1, with the exception that 269.9 parts of acetoacetic acid m-xylidide and 135.4 parts of acetoacetic acid o-toluidide were used, instead of the 415 parts of acetoacetic acid m-xylidide.
  • This disazo pigment corresponded to a rosin-treated, disazo pigment (including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)), obtained by reacting 65 mol% of acetoacetic acid m-xylidide and 35 mol% of acetoacetic acid o-toluidide, as the mixed coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a rosin-treated, disazo pigment including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)
  • a powdered disazo pigment (Disazo Pigment 5) was obtained, in the same manner as in the manufacturing of a disazo pigment according to Disazo Pigment Manufacturing Example 1, with the exception that 83.1 parts of acetoacetic acid m-xylidide and 309.5 parts of acetoacetic acid o-toluidide were used, instead of the 415 parts of acetoacetic acid m-xylidide.
  • This disazo pigment corresponded to a rosin-treated, disazo pigment (including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)), obtained by reacting 20 mol% of acetoacetic acid m-xylidide and 80 mol% of acetoacetic acid o-toluidide, as the mixed coupler components, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a rosin-treated, disazo pigment including a compound with an identical chemical structure to that of C. I. Pigment Yellow 13, a compound with an identical chemical structure to that of C. I. Pigment Yellow 14, and a compound represented by Formula (I)
  • a powdered disazo pigment (Disazo Pigment 6) was obtained, in the same manner as in the manufacturing of a disazo pigment according to Disazo Pigment Manufacturing Example 1, with the exception that 386.9 parts of acetoacetic acid o-toluidide were used, instead of the 415 parts of acetoacetic acid m-xylidide.
  • This disazo pigment corresponded to a rosin-treated, disazo pigment (C. I. Pigment Yellow 14), obtained by reacting 100 mol% of acetoacetic acid o-toluidide, as the coupler component, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • C. I. Pigment Yellow 14 a rosin-treated, disazo pigment obtained by reacting 100 mol% of acetoacetic acid o-toluidide, as the coupler component, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a powdered disazo pigment (Disazo Pigment 7) was obtained, in the same manner as in the manufacturing of a disazo pigment according to Disazo Pigment Manufacturing Example 1, with the exception that 386.9 parts of acetoacetic acid p-toluidide were used, instead of the 415 parts of acetoacetic acid m-xylidide.
  • This disazo pigment corresponded to a rosin-treated, disazo pigment (C. I. Pigment Yellow 55), obtained by reacting 100 mol% of acetoacetic acid p-toluidide, as the coupler component, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • C. I. Pigment Yellow 55 a rosin-treated, disazo pigment obtained by reacting 100 mol% of acetoacetic acid p-toluidide, as the coupler component, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • a mill base was prepared using a laboratory mixer, by means of mixing a pigment composition, formed by mixing 95 parts of Disazo Pigment 1 and 5 parts of Disazo Compound Mixture 1, in a stainless steel container containing 300 parts of varnish (containing a rosin-modified phenol resin), which had been heated to 40°C.
  • a base ink was then prepared by means of milling this mill base using a triple-roll mill.
  • a test ink was then prepared by means of gradually adding 170 parts of varnish for a lithographic ink and 5 parts of light oil to the aforementioned base ink while running the triple-roll mill.
  • a mill base was prepared using a laboratory mixer, by means of mixing a pigment composition, formed by mixing 95 parts of Disazo Pigment 1 and 5 parts of Comparative Disazo Compound Mixture 1, in a stainless steel container containing 300 parts of varnish (containing a rosin-modified phenol resin), which had been heated to 40°C.
  • a base ink was then prepared by means of milling this mill base using a triple-roll mill.
  • a test ink was then prepared by means of gradually adding 170 parts of varnish for a lithographic ink and 5 parts of light oil to the aforementioned base ink while running the triple-roll mill.
  • a mill base was prepared using a laboratory mixer, by means of mixing a pigment composition, formed by mixing 95 parts of Disazo Pigment 1 and 5 parts of Comparative Disazo Compound Mixture 2, in a stainless steel container containing 300 parts of varnish (containing a rosin-modified phenol resin), which had been heated to 40°C.
  • a base ink was then prepared by means of milling this mill base using a triple-roll mill.
  • a test ink was then prepared by means of gradually adding 170 parts of varnish for a lithographic ink and 5 parts of light oil to the aforementioned base ink while running the triple-roll mill.
  • a mill base was prepared using a laboratory mixer, by means of mixing a pigment composition, formed by mixing 95 parts of Disazo Pigment 1 and 5 parts of Comparative Disazo Compound Mixture 3, in a stainless steel container containing 300 parts of varnish (containing a rosin-modified phenol resin), which had been heated to 40°C.
  • a base ink was then prepared by means of milling this mill base using a triple-roll mill.
  • a test ink was then prepared by means of gradually adding 170 parts of varnish for a lithographic ink and 5 parts of light oil to the aforementioned base ink while running the triple-roll mill.
  • the flow ability on a glass plate was evaluated by lightly mixing and applying a test ink, using a spatula, to the higher end of a glass plate which was inclined to an angle of 70°, allowing the test ink to sit for one hour, and then measuring the distance to the leading edge of the ink which had run towards the lower end.
  • High measured values for the glass plate flow ability indicate a high flow ability.
  • the measured values obtained above are displayed as a percentage, with the test inks obtained in each Test Example designated as 100%.
  • test ink was transferred to a white transfer paper onto which a black band had been printed using black ink, and the transferred state of the ink on the black band was evaluated by visual observation.
  • the test ink was judged to be opaque, and given a score of 1.
  • the test ink was judged as transparent, and given a score of 5.
  • Test Sample Glass plate flow ability Transparency Test Example 2 100% 4 Comparative Test Example 2-1 22% 4 Comparative Test Example 2-2 64% 4 Comparative Test Example 2-3 56% 4
  • Test Sample Glass plate flow ability Transparency Test Example 3 100% 5 Comparative Test Example 3-1 25% 5 Comparative Test Example 3-2 56% 5 Comparative Test Example 3-3 57% 5
  • Test Sample Glass plate flow ability Transparency Test Example 6 100% 2 Comparative Test Example 6-1 75% 2 Comparative Test Example 6-2 36% 2 Comparative Test Example 6-3 40% 2
  • a disazo compound mixture (Disazo Compound Mixture 2) was obtained, in the same manner as in the manufacturing of a disazo compound mixture according to Disazo Compound Mixture Manufacturing Example 1, with the exception that 28.7 parts of 2-acetoacetylamino benzoic acid, 27.9 parts of acetoacetic acid m-xylidide, and 6.9 parts of acetoacetic acid o-toluidide were used instead of the 26.7 parts of 2-acetoacetylamino benzoic acid, 26.0 parts of acetoacetic acid m-xylidide, and 10.4 parts of acetoacetic acid o-toluidide.
  • This disazo compound mixture corresponded to a disazo compound mixture obtained by reacting 45 mol% of acetoacetic acid m-xylidide, 12 mol% of acetoacetic acid o-toluidide, and 43 mol% of 2-acetoacetylamino benzoic acid, as the mixed coupler component, with a tetrazo compound of 3,3'-dichlorobenzidine, as the tetrazo component.
  • the test inks obtained in Test Examples 1 to 8, which were prepared by means of using the pigment composition according to the present invention, are regarded as printing inks exhibiting a superior flow ability.
  • the test inks according to the conventional methods, obtained in Comparative Test Examples 1-1 to 8-3, are regarded as printing inks displaying an inferior flow ability.
  • the composition i.e., an additive for a disazo pigment
  • a disazo compound mixture comprising a disazo compound mixture according to the present invention
  • the pigment composition containing a disazo pigment, and the composition comprising said disazo compound mixture is able to provide a printing ink with a superior flow ability.
  • the present invention provides an additive for a disazo pigment comprising a disazo compound mixture, which is obtained by means of reacting specific coupler components, with a specific molar ratio, and thus possesses a desirable dispersability compared to the conventional disazo pigments, when mixed and used with a disazo pigment. Therefore, in the same manner as above, the pigment composition containing a disazo pigment, and the composition comprising said disazo compound mixture, is able to provide a printing ink with a superior flow ability.
  • the resultant printing ink possesses a high transparency, and is able to produce printed matter more clearly.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Claims (9)

  1. Additif pour un pigment diazoïque contenant au moins les composés diazoïques suivants représentés respectivement par les Formules (I), (IV) et (V)
    Figure 00480001
    Figure 00480002
    Figure 00480003
  2. Additif pour un pigment diazoïque contenant les composés diazoïques représentés par les Formules (I) à (VI) suivantes:
    Figure 00490001
    Figure 00490002
    Figure 00490003
    Figure 00500001
    Figure 00500002
    Figure 00500003
  3. Additif pour un pigment diazoïque selon la revendication 1 et la revendication 2, dans lequel est contenue une plus grande quantité du composé diazoïque représenté par la Formule (V) que dudit composé diazoïque représenté par la Formule (IV).
  4. Additif pour un pigment diazoïque contenant six types de composés diazoïques, qui est formé par la réaction de m-xylidide de l'acide acétoacétique, d'o-toluidide de l'acide acétoacétique et d'acide 2-acétoacétylaminobenzoïque en tant que composants de copulation, avec un composé tétrazoïque de la 3,3'-dichlorobenzidine en tant que composant tétrazoïque.
  5. Additif pour un pigment diazoïque selon la revendication 4, dans lequèl le rapport molaire desdits composants de copulation correspondant à 39 à 47 % molaire de m-xylidide de l'acide acétoacétique, à 11 à 19 % molaire d'o-toluidide de l'acide acétoacétique et à 38 à 46 % molaire d'acide 2-acétoacétylaminobenzoïque.
  6. Additif pour un pigment diazoïque selon l'une quelconque des revendications 1, 2, 3, 4 et 5 dans lequel ledit additif n'est pas traité avec de la rosine.
  7. Additif pour un pigment diazoïque selon l'une quelconque des revendications 1, 2, 3, 4, 5 et 6, et pigment diazoïque.
  8. Composition pigmentaire diazoïque comprenant un additif selon l'une quelconque des revendications 1, 2, 3, 4, 5 et 6, et un pigment diazoïque traité à la rosine.
  9. Composition pigmentaire diazoïque selon la revendication 7 ou la revendication 8, dans laquelle ledit pigment diazoïque est au moins un pigment diazoïque choisi au sein du groupe comprenant le Pigment Jaune C.I. 13, le Pigment Jaune C.I. 14 et un composé diazoïque représenté par la Formule (I).
EP99108579A 1998-05-11 1999-05-06 Additif pour pigment comprenant des composés disazoiques et compositions pigmentaires le contenant Expired - Lifetime EP0957136B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP12733598 1998-05-11
JP12733598 1998-05-11

Publications (3)

Publication Number Publication Date
EP0957136A2 EP0957136A2 (fr) 1999-11-17
EP0957136A3 EP0957136A3 (fr) 2000-02-23
EP0957136B1 true EP0957136B1 (fr) 2001-12-05

Family

ID=14957385

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99108579A Expired - Lifetime EP0957136B1 (fr) 1998-05-11 1999-05-06 Additif pour pigment comprenant des composés disazoiques et compositions pigmentaires le contenant

Country Status (3)

Country Link
EP (1) EP0957136B1 (fr)
CN (1) CN1101840C (fr)
DE (1) DE69900521T2 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6667392B2 (en) * 2000-11-29 2003-12-23 Milliken & Company Polymeric acetoacetanilide azo colorants
ES2376465T3 (es) * 2005-11-28 2012-03-14 Agfa Graphics N.V. Dispersiones de pigmentos no acuosas que contienen sinergistas de dispersión espec�?ficos.
EP1790696B1 (fr) 2005-11-28 2013-04-10 Agfa Graphics N.V. Dispersions de pigment non-aqueuses contenant des synergistes de dispersion spécifiques
JP5172229B2 (ja) * 2007-07-04 2013-03-27 住友化学株式会社 アゾ化合物又はその塩
CN101942209B (zh) * 2010-08-21 2013-03-20 维波斯新材料(潍坊)有限公司 用4-乙酰乙酰氨基苯膦酸盐改性的偶氮黄色颜料的制备方法
CN103387752A (zh) * 2013-07-31 2013-11-13 瑞安宝源化工有限公司 一种p.y.13永固黄颜料的制备工艺
CN109593381A (zh) * 2018-12-29 2019-04-09 瑞安宝源化工有限公司 高透明度高流动颜料永固黄174的制备方法
CN109705611A (zh) * 2018-12-29 2019-05-03 瑞安宝源化工有限公司 环保节能型颜料永固黄13的制备方法
CN110499041B (zh) * 2019-08-19 2021-04-16 宇虹颜料股份有限公司 易过滤的eva蜡基复合球状颜料黄14的制备方法
JP7173352B2 (ja) * 2020-06-28 2022-11-16 Dic株式会社 顔料組成物、印刷インキ、及び顔料組成物の製造方法
CN115772336B (zh) * 2022-11-15 2024-02-20 双乐颜料泰兴市有限公司 一种紫色有机颜料的制备

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63178169A (ja) * 1987-01-17 1988-07-22 Dainippon Ink & Chem Inc ジスアゾ顔料組成物
JPH04275373A (ja) * 1991-03-01 1992-09-30 Toyo Ink Mfg Co Ltd ジスアゾ顔料および印刷インキ組成物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2012152C3 (de) * 1970-03-14 1974-03-21 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Verfahren zur Herstellung von Pigmentfarbstoffgemischen aus Disazofarbstoffen und deren Verwendung
JPS6023552B2 (ja) * 1978-10-05 1985-06-07 シャープ株式会社 画像信号処理装置
US4648907A (en) * 1985-04-12 1987-03-10 Basf Corporation High color strength diarylide yellow pigment compositions
DE3630278A1 (de) * 1986-09-05 1988-03-17 Basf Lacke & Farben Disazoverbindungen und diese disazoverbindungen enthaltenden zubereitungen
GB9117292D0 (en) * 1991-08-09 1991-09-25 Ciba Geigy Ag Coupling process
IN192574B (fr) * 1996-08-08 2004-05-01 Dainippon Ink & Chemicals

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63178169A (ja) * 1987-01-17 1988-07-22 Dainippon Ink & Chem Inc ジスアゾ顔料組成物
JPH04275373A (ja) * 1991-03-01 1992-09-30 Toyo Ink Mfg Co Ltd ジスアゾ顔料および印刷インキ組成物

Also Published As

Publication number Publication date
EP0957136A3 (fr) 2000-02-23
EP0957136A2 (fr) 1999-11-17
CN1235177A (zh) 1999-11-17
CN1101840C (zh) 2003-02-19
DE69900521T2 (de) 2002-05-23
DE69900521D1 (de) 2002-01-17

Similar Documents

Publication Publication Date Title
JP4861899B2 (ja) Ｃ．ｉ．ピグメントレッド５７：１及びその製造方法
EP0957136B1 (fr) Additif pour pigment comprenant des composés disazoiques et compositions pigmentaires le contenant
CN1942531B (zh) 流变学改善的油墨用颜料组合物
TW200918610A (en) Pigment preparations based on C. I. pigment blue 15:6
JP4759966B2 (ja) モノアゾレーキ顔料組成物の製造方法
JPH04180969A (ja) モノアゾレーキ顔料およびその用途
JPH03163169A (ja) モノアゾレーキ顔料、その製造方法および顔料分散体
US5190585A (en) Production of pigment compositions
JP4362887B2 (ja) ジスアゾ顔料添加剤および顔料組成物
JP4161238B2 (ja) 顔料組成物及び顔料分散体
EP0952191B1 (fr) Composition de pigment disazoique , encres d'impression contenant une telle composition et une méthode pour la préparer
JP3170697B2 (ja) 顔料分散剤
JP3561847B2 (ja) 顔料分散剤および顔料組成物
JP2006299050A (ja) 顔料分散剤およびこれを含む顔料組成物
JP2629070B2 (ja) 銅フタロシアニン顔料組成物およびそれを用いた顔料分散体組成物
GB2051108A (en) Continuous Method of Producing Aqueous Phthalocyanine Pigment Dispersions
JP3428491B2 (ja) ジスアゾ顔料組成物の製造方法
JPS63120764A (ja) モノアゾレーキ顔料の製造方法
CN101457030A (zh) 高档紫色颜料及其制备方法
JP3544121B2 (ja) 顔料組成物及びそれを含むインキ
JPH04146969A (ja) モノアゾレーキ顔料および印刷インキ組成物
JP2002338841A (ja) アゾレーキ顔料、アゾレーキ顔料の製造方法及び印刷インキ
JP2696060B2 (ja) オフセットインキ用顔料水ペーストの製造方法
GB2324097A (en) Pigment preparation in pellet form
JPH1088016A (ja) アゾレーキ顔料組成物、その製造方法および顔料分散体

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): DE FR GB

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

RIC1 Information provided on ipc code assigned before grant

Free format text: 7C 09B 67/22 A, 7C 09D 11/02 B

17P Request for examination filed

Effective date: 20000608

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

AKX Designation fees paid

Free format text: DE FR GB

17Q First examination report despatched

Effective date: 20001106

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

REF Corresponds to:

Ref document number: 69900521

Country of ref document: DE

Date of ref document: 20020117

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 17

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 18

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 19

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20180329

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20180424

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20180411

Year of fee payment: 20

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 69900521

Country of ref document: DE

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20190505

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20190505